Masterclass, the website offering video-based “lessons” in many professions and arts by admired celebrities and well-known experts, is one of those great ideas that cause entrepreneurs to moan with a certain degree of envy, admiration, and feigned disbelief. The business is itself a lesson in innovation hiding in plain sight: providing “students” of every age and interest with the opportunity to learn from their favorite actor, inventor, or avatar.
But what specifically does Masterclass and its founder and CEO David Rogier have to offer the leaders of the freelance revolution?
Let’s start with fundamentals: what’s made Masterclass a success. For over 100 years, public relations professionals have taught us that messages delivered by relevant celebrities or respected experts– people we know and admire – are particularly persuasive. Applying that insight to education at scale was brilliant. And, lubricated by the unique conditions of Covid, an exceptionally prodigious accelerant.
Imagine learning how to understand the economy with Nobelist Paul Krugman, how to write with Margaret Atwood, cooking with Alice Waters, or learning how to appreciate art more deeply with art legend Jeff Koons.
Rogier believed a business that combined relevant education with top production values and amazing “teachers” offered a successful formula. There had been earlier experiments; for example, Monty Python’s star John Cleese created a successful business educational film company Videoarts fifty years earlier. Other educationally based internet companies like Jolt.io were starting up around the same time, but Masterclass was the first to fuse Silicon Valley tech with Hollywood style.
Masterclass rode the internet to a new level of scale fueled by the pandemic. Just 8 years since the company’s formation, it boasts millions of subscribers engaging in videos taught by a unique range of experts and celebrities. From Noam Chomsky on independent thinking to Carlos Santana on the art of the guitar, and just about everything in between that a life-long student might find of interest. More than that, many subscribers attest to the impact of Masterclass in their personal lives: according to Tech Crunch, a quarter of the Gen Z and Millenials who primarily make up Masterclass subscribers say that Masterclass courses have changed their lives.
There has been plenty written about Masterclass that needn’t be repeated. And, like other successes, the concept (“What if you could learn from the best in any field?”) and execution has taken its share of digs from the odd cynical journalist. For example, an Atlantic article unfairly opined, “Having someone of Thomas Keller’s stature teaching the basics of cooking is impressive, but is it necessary? You can learn useful things by watching a video, but formal education is generally understood to demand some kind of participation, as well as a teacher evaluation. Some instructors host promotional contests with student participation—in one case, James Patterson co-wrote a book with a student—but in general, Malcolm Gladwell isn’t going to grade your essay, nor is Thomas Keller going to evaluate your meringue.”
Nevertheless, Masterclass has proven to be a durable commercial juggernaut, with $400 million in investment, a valuation in the billions, and a top creative team.
Great business builders are often equal parts visionary and philosophical about their success. Rogier no different. He is open about what’s worked, hasn’t, and what trials and errors eventually created a winner. So, what has Rogier learned of value to current and future entrepreneurs? Over two recent conversations, the second while on his way to 2023 SXSW, Rogier generously shared the insights he’s learned in building the business. Four seemed to be particularly helpful:
“If it’s not interesting to you, it won’t be to anyone else.” Following an internship at IDEO and four years after his MBA at Stanford, Rogier created the predecessor firm that led to Masterclass. His north star for Masterclass was to create something “important, relevant, and meaningful.” When asked in a recent Bloomberg interview with Emily Chang, he put it this way. “I’m excited about the classes that help me – and others – change how I think about the world. For example, a recent class by Hans Zimmer literally changed how I now hear music.” Rogier reminds to, first and foremost, make sure products and services we freelancers offer are worthy of our clients. Freelance platform entrepreneurs, are you stretching to create what Steve Jobs called ‘insanely great’ or just to place somewhere on the board?
“Don’t be blinded by success or failure.” Part of Rogier’s message is to keep making it better. It takes 4-5 months to organize, plan, script, shoot, and finish an educational video before its ready for prime time. “There’s no part of Masterclass that’s able to rest on its laurels,” Roger pointed out. But he also made it clear that the flip side – don’t let failure get under your skin – is of equal importance. He put it this way: “Sometimes fabulously successful people haven’t really explained to themselves what made them successful. For example, when Sarah Barkley who famously founded Spanx was finished shooting the lesson, she began to tear up. She never stopped believing she was on the right track, despite many early disappointments.” Freelance platform entrepreneurs, are you driven to keep making the product, service, or experience better while remaining committed to your vision? The discovery tour that Brian Chesky of Airbnb famously took both reinforced his belief in Airbnb while leading him to reinvent much of the service.
“The best classes deliver in multiple ways.” Rogier frequently mentions the negotiator Chris Voss’s lesson on crisis negotiation as a best seller. “Why?” he rhetorically asks, “It’s profoundly dramatic, but also teaches widely applicable lessons about how to deal with any negotiation in business or life. Or Gordon Ramsey who, in a lesson on cooking, reminded students that “In cooking and in life, don’t learn on an expensive salmon; learn on a trout. It’s cheaper.” Freelance entrepreneurs, are you leveraging the full potential of each client and talent relationship? As Chef Ramsey points out, have you established a discipline for moving the business forward step by step?
“Your talent has to get as much out of the work as your clients.” If you are a freelance entrepreneur, talent is your service. In most freelance platforms, the outcomes are too often lopsided. Many freelancers are offered little help by their marketplace in finding work or building their skills. Rogier pointed out that the best lessons, and his best strategy for attracting icons and experts, is to make sure they get as much or more from the collaboration. For some, in addition to the financial benefit, it’s the chance to give back through teaching at scale. For others it’s the personal reflection, the potential to change people’s lives, or simply a wish to share what they know or what they have learned. Freelance entrepreneurs, top talent will join your platform if it’s worth their while to do so. 10XManagement co-CEO Rishon Blumberg says, “We think of our talent as clients, just as we think of companies as our customers. They are equally important to serve well.” Are you set up and committed to deliver the best experience to your talent?
Masterclass has continued to grow and mature. Post Covid, the company remains among the most successful educational startups. Now with a huge subscriber base, a much larger organization, and strong funding, Rogier’s CEO challenge is to apply these lessons to the next stage of Masterclass growth. He’s already taken some of the steps one might expect from a CEO who is always looking for the force multiplier.
For example, it’s now finding new channels for its content, like streaming on Delta Airlines. Masterclass is also creating corporate subscriber relationships through Masterclass for Business, and current users include half of the Fortune 100 companies. The company is increasingly aware of how to fully benefit from its content. For example, it is now converting long classes into shorter programs that enable members to combine a collection of lessons to assemble a curriculum. A budding singer might combine a Christina Aguilera lesson on “Singing” with Timbaland’s lesson on “Producing” with Usher’s class on “Performing.” Wow!
Viva la revolution!
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